Jesse, a charming and romantic individual, struggles with the concept of marriage despite being excellent at proposing. After a recent breakup with Hannah and the unexpected passing of a former fiancée, he embarks on a journey to understand what went wrong in his past relationships. He seeks advice from his former flames, including his teenage sweetheart, a group of lesbians, and even his deceased former fiancée Anabeth, who appears to him in his dreams. With the help of his friends and colleagues, Jesse is able to reconnect with an ex who is still furious with him. He attends Anabeth's funeral, where he will encounter Hannah once again and hopefully gain a deeper understanding of his own feelings and what he truly desires.
Seven Girlfriends
A man's attempt to propose is met with a harsh reality check: he's clueless about relationships. In a quest for self-discovery, he embarks on a journey to reconnect with his seven former girlfriends, hoping to uncover the secrets to a successful partnership.